Agomelatine (CED0004638)

Record Information

Version

1.0

Creation Date

2016-05-22 07:17:30 UTC

Update Date

2026-08-19 10:40:56 UTC

Accession Number

CHEM020641

Identification

Common Name

Agomelatine

Class

Small Molecule

Description

Agomelatine is an organic compound with the formula C15H17NO2 and an average molecular weight of 243.30 g/mol. Agomelatine belongs to the carboxylic acid derivatives, a subclass of carboxylic acids and derivatives within the organic compounds. This compound is recorded as being found in or released from two sources: indoor air (air, dust & atmospheric transport) and antidepressants (healthcare, pharmaceuticals & veterinary products). Exposure routes for agomelatine include oral and inhalation. In terms of biological activity, the compound has three recorded protein targets, acting as an agonist or antagonist of the melatonin receptor type 1A (MTNR1A), melatonin receptor type 1B (MTNR1B), and 5-hydroxytryptamine receptor 2C (HTR2C).

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Valdoxan	Kegg
S-20098	HMDB
S20098	HMDB
N-(2-(7-Methoxy-1-naphthyl)ethyl)acetamide	HMDB
Thymanax	HMDB
Ago 178	HMDB
Ago-178	HMDB

Chemical Formula

C₁₅H₁₇NO₂

Average Molecular Mass

243.301 g/mol

Monoisotopic Mass

243.126 g/mol

CAS Registry Number

138112-76-2

IUPAC Name

N-[2-(7-methoxynaphthalen-1-yl)ethyl]acetamide

Traditional Name

agomelatine

SMILES

COC1=CC2=C(C=CC=C2CCNC(C)=O)C=C1

InChI Identifier

InChI=1S/C15H17NO2/c1-11(17)16-9-8-13-5-3-4-12-6-7-14(18-2)10-15(12)13/h3-7,10H,8-9H2,1-2H3,(H,16,17)

InChI Key

YJYPHIXNFHFHND-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as n-acetyl-2-arylethylamines. N-acetyl-2-arylethylamines are compounds containing an acetamide group that is N-linked to an arylethylamine.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Carboxylic acid derivatives

Direct Parent

N-acetyl-2-arylethylamines

Alternative Parents

Substituents

N-acetyl-2-arylethylamine
Naphthalene
Anisole
Alkyl aryl ether
Benzenoid
Secondary carboxylic acid amide
Ether
Organic oxide
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Organic nitrogen compound
Carbonyl group
Organic oxygen compound
Hydrocarbon derivative
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Organoleptic Effects

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.0078 g/L	ALOGPS
logP	2.83	ALOGPS
logP	2.04	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	15.96	ChemAxon
pKa (Strongest Basic)	-0.94	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	38.33 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	71.64 m³·mol⁻¹	ChemAxon
Polarizability	27.18 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum	splash10-0096-9870000000-12644f5c2eef8ac161ff	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-000i-1910000000-17cebfbe6b9845617b5d	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0udl-0290000000-2f32e7333df35f0d31e0	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0udi-1890000000-f8670d6acc856a2aef34	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-103c-1900000000-44f5e0bbe33a080e259b	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0006-1190000000-60e7560fd8d53fc46465	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0zfu-3590000000-b1f2b056df1b588a9894	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-052f-9200000000-7d7eb2751fc51b48fda4	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-000l-0960000000-1b1a339607ebe3d5742f	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-000i-0900000000-84ce72fe2cc1bb7fae00	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0a4i-1900000000-0471137531ade7533965	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00di-0910000000-64f66595ca495c9bd240	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0a4i-1900000000-5cf1d78282a06e7b1962	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0a4l-5900000000-9ed4ac12ad0427b40af3	Not Available	View Spectrum

Toxicity Profile

Mechanism of Toxicity

Not Available

Carcinogenicity (IARC Classification)

Not Available

Minimum Risk Level

Not Available

Symptoms

Not Available

Treatment

Not Available

Toxicity Values

Toxicity Value	Unit	Value Range	Organism	Dose Descriptor	Route of Exposure	Predicted or Experimental	Reference
1196.0	Log mg/kg	[670:2100]	Rat	LD50	oral	predicted	Not Available

Health Effects

Health Effect	Relationship	Direction	Reference

Exposure Sources

Source ID	Source	Sector	Reference
19	Indoor air	Air, dust & atmospheric transport	Not Available
377	Antidepressants	Healthcare, pharmaceuticals & veterinary products	Not Available

Pathways

3 pathways

Agomelatine Serotonin Antagonist Action Pathway

Agomelatine Drug Metabolism Action Pathway

Agomelatine Predicted Metabolism Pathway

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	Melatonin receptor type 1A	P48039	Humans	Predicted (SEA)	0.0778492
Click to view 3D structure	Melatonin receptor type 1B	P49286	Humans	Predicted (SEA)	0.0778492
Click to view 3D structure	Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	Humans	Predicted (SEA)	0.0778492
Click to view 3D structure	Melatonin receptor type 1C	P49219	Xenopus laevis	Predicted (SEA)	0.389246
Click to view 3D structure	Melatonin receptor type 1B	P51050	Gallus gallus	Predicted (SEA)	0.778492
Click to view 3D structure	5-hydroxytryptamine receptor 2C	P28335	Humans	Predicted (SEA)	88.281
Click to view 3D structure	Prostaglandin G/H synthase 1	P23219	Humans	Predicted (SEA)	25.6902
Click to view 3D structure	Acetylcholinesterase	P23795	Bos taurus	Predicted (SEA)	18.2946
Click to view 3D structure	Aldo-keto reductase family 1 member C3	P42330	Humans	Predicted (SEA)	15.492
Click to view 3D structure	Histamine H3 receptor	Q9Y5N1	Humans	Predicted (SEA)	116.151
Click to view 3D structure	Butyrylcholinesterase	Q9N1N9	Equus caballus	Predicted (SEA)	21.9535
Click to view 3D structure	Cholinesterase	P06276	Humans	Predicted (SEA)	98.5571
Click to view 3D structure	Cholinesterase	P81908	Equus caballus	Predicted (SEA)	113.426
Click to view 3D structure	Aldo-keto reductase family 1 member C2	P52895	Humans	Predicted (SEA)	18.061
Click to view 3D structure	5-hydroxytryptamine receptor 2B	P41595	Humans	Predicted (SEA)	229.5
Click to view 3D structure	Cytochrome P450 1A2	P05177	Humans	Predicted (SEA)	302.6
Click to view 3D structure	Acetylcholinesterase	P22303	Humans	Predicted (SEA)	192.054
Click to view 3D structure	G-protein coupled receptor 35	Q9HC97	Humans	Predicted (SEA)	12.6894
Click to view 3D structure	Sodium-dependent noradrenaline transporter	P23975	Humans	Predicted (SEA)	173.059
Click to view 3D structure	Carbonic anhydrase 12	O43570	Humans	Predicted (SEA)	160.681
Click to view 3D structure	Carbonic anhydrase 14	Q9ULX7	Humans	Predicted (SEA)	83.7658
Click to view 3D structure	Prostaglandin G/H synthase 2	P35354	Humans	Predicted (SEA)	87.9696
Click to view 3D structure	Vascular endothelial growth factor receptor 2	P35968	Humans	Predicted (SEA)	877.828
Click to view 3D structure	5-hydroxytryptamine receptor 6	P50406	Humans	Predicted (SEA)	260.483
Click to view 3D structure	5-hydroxytryptamine receptor 1A	P08908	Humans	Predicted (SEA)	426.536